One-pot synthesis of selenoureas and selenocarbamates via selenation of isocyanates with bis(dimethylaluminum) selenide

Tetrahedron Letters

Volumn 52, Issue 3, 2011, Pages 415-417

  Maeda, Hajime ^a   Takashima, Masaru ^a   Sakata, Koichi ^a   Watanabe, Tatsuya ^a   Honda, Mitsunori ^a   Segi, Masahito ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BIS(DIMETHYLALUMINUM)SELENIDE; CARBAMIC ACID DERIVATIVE; ISOCYANIC ACID DERIVATIVE; SELENIDE; SELENIUM DERIVATIVE; SELENOCARBAMATE; SELENOUREA; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; DRUG MIXTURE; ONE POT SYNTHESIS; SELENATION; STOICHIOMETRY;

EID: 78650253407     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.069     Document Type: Article

References (37)

1. M. Segi, and S. Suga J. Synth. Org. Chem., Jpn. 48 1990 1064 1065
2. M. Segi, and T. Nakajima J. Synth. Org. Chem., Jpn. 53 1995 678 686
3. M. Segi, T. Koyama, T. Nakajima, S. Suga, S. Murai, and N. Sonoda Tetrahedron Lett. 30 1989 2095 2098
4. G.M. Li, M. Segi, and T. Nakajima Tetrahedron Lett. 33 1992 3515 3518
5. G.M. Li, S. Niu, M. Segi, R.A. Zingaro, H. Yamamoto, K. Watanabe, T. Nakajima, and M.B. Hall J. Org. Chem. 64 1999 1565 1575
6. A. Zhou, M. Segi, and T. Nakajima Tetrahedron Lett. 44 2003 1179 1182
7. M. Segi, A. Zhou, and M. Honda Phosphorus, Sulfur, Silicon 180 2005 1045 1049
8. M. Segi, K. Tanno, M. Kojima, M. Honda, and T. Nakajima Tetrahedron Lett. 48 2007 2303 2306
9. M. Segi, A. Kojima, T. Nakajima, and S. Suga Synlett 1991 105 106
10. G.M. Li, R.A. Zingaro, M. Segi, J.H. Reibenspies, and T. Nakajima Organometallics 16 1997 756 762
11. M. Segi, T. Takahashi, H. Ichinose, G.M. Li, and T. Nakajima Tetrahedron Lett. 33 1992 7865 7868
12. G.M. Li, T. Kamogawa, M. Segi, and T. Nakajima Chem. Express 8 1993 53 56
13. 4, and evaporated in vacuo. Purification by silica gel column chromatography gave pure isoselenocyanates.
14. 2O with RONa may be involved.
15. J. Gilmore, and P.T. Gallagher A.R. Katritzky, O. Meth-Cohn, C.W. Rees, Comprehensive Organic Functional Group Transformations Vol. 5 1995 Pergamon Oxford 1021 1059
16. F.S. Guziec Jr. S. Patai, The Chemistry of Organic Selenium and Tellurium Compounds Vol. 2 1987 John Wiley & Sons New York 215 273
17. A. Toshimitsu, and S. Uemura S. Patai, The Chemistry of Organic Selenium and Tellurium Compounds Vol. 2 1987 John Wiley & Sons New York 541 590
18. E. Bulka, and K.-D. Ahlers Z. Chem. 3 1963 348 349
19. N. Sonoda, G. Yamamoto, and S. Tsutsumi Bull. Chem. Soc. Jpn. 45 1972 2937 2938
20. T.G. Back, D.H.R. Barton, M.R. Britten-Kelly, and F.S. Guziec Jr. J. Chem. Soc., Perkin Trans. 1 1976 2079 2089
21. D.H.R. Barton, S.I. Parekh, M. Tajbakhsh, E.A. Theodorakis, and C.-L. Tse Tetrahedron 50 1994 639 654
22. J.G. Fernández-Bolaños, o. López, V. Ulgar, I. Maya, and J. Fuentes Tetrahedron Lett. 45 2004 4081 4084
23. I.B. Douglass J. Am. Chem. Soc. 59 1937 740 742
24. C.Th. Pedersen Acta Chem. Scand. 17 1963 1459 1461
25. N.A. Kirsanova, and G.I. Derkach Ukr. Khim. Zh. (Russ. Ed.) 36 1970 372 374 Chem. Abstr. 1970, 73, 445417q
26. W.J. Stec, K. Lesiak, and M. Sudol Synthesis 1975 785 787
27. S. Uemura, N. Watanabe, A. Toshimitsu, and M. Okano Bull. Chem. Soc. Jpn. 51 1978 1818 1820
28. Y. Tamura, M. Adachi, T. Kawasaki, and Y. Kita Tetrahedron Lett. 20 1979 2251 2252
29. T. Tarantelli, and D. Leonesi Ann. Chim. (Rome) 53 1963 1113 1122
30. H. Suzuki, M. Usuki, and T. Hanafusa Synthesis 1979 705 707
31. M.V. Andreocci, M. Bossa, C. Furlani, M.N. Piancastelli, C. Cauletti, and T. Tarantelli J. Chem. Soc., Faraday Trans. 2 75 1979 105 112
32. L. Henriksen Int. J. Sulfur Chem. 8 1973 389 396
33. L. Henriksen, and U. Ehrbar Synthesis 1976 519 521
34. S. Tanaka, S. Uemura, and M. Okano Bull. Chem. Soc. Jpn. 50 1977 722 725
35. D.L. Klayman, J.P. Scovill, J.F. Bartosevich, and C.J. Mason Eur. J. Med. Chem. 16 1981 317 320
36. T.G. Back, and R.G. Kerr J. Organomet. Chem. 286 1985 171 182
37. C. Collard-Charon, and M. Renson Bull. Soc. Chim. Berg. 71 1962 531 540